disodium (2S)-3-(1H-indol-3-yl)-2-[(2S)-4-methyl-2-[({[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphinato)amino]pentanamido]propanoate

• ChemBase ID: 134165
• Molecular Formular: C23H32N3Na2O10P
• Molecular Mass: 587.467581
• Monoisotopic Mass: 587.16206943
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OP(=O)(N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)[O-])[O-])O)O)O.[Na+].[Na+]
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)[O-])Cc1c[nH]c2c1cccc2)NP(=O)(O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)[O-])C.[Na+].[Na+]
• InChI: InChI=1S/C23H34N3O10P.2Na/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15;;/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34);;/q;2*+1/p-2/t12-,16-,17-,18-,19+,20+,23-;;/m0../s1
• InChIKey: OQKHVXFOYFBMDJ-ODIUWQMJSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S)-3-(1H-indol-3-yl)-2-[(2S)-4-methyl-2-[({[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphinato)amino]pentanamido]propanoate
• IUPAC Traditional name: disodium (2S)-3-(1H-indol-3-yl)-2-[(2S)-4-methyl-2-({[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphinato}amino)pentanamido]propanoate
• Synonyms: N-(α-Rhamno-pyranosyl-oxy-hydroxy-phosphinyl)-Leu-Trp disodium salt; N-(α-Rhamno-pyranosyl-phos-phono)-L-leucyl-L-tryptophan disodium salt; Phosphoramidon disodium salt

Database IDs

• CAS Number: 119942-99-3
• MDL Number: MFCD00077870
• Beilstein Number: 8105669
• PubChem SID: 162228442; 24278681
• PubChem CID: 16219931

CALCULATED PROPERTIES

• Acid pKa: 2.48479
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -3.6547024
• LogD (pH = 7.4): -5.3870897
• Log P: 0.15903191
• Molar Refractivity: 138.6551 cm^3
• Polarizability: 52.22761 Å^3
• Polar Surface Area: 216.33 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetic acid: soluble20 mg/mL, clear, colorless to light yellow-green; DMSO: soluble; H2O: soluble1 mM (Stock solution stable for 1 month at –20° C.); methanol: soluble

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (TLC); ≥97.0% (TLC)
• Impurities: ≤6% water
• Empirical Formula (Hill Notation): C23H32N3Na2O10P

DETAILS

Sigma Aldrich - R7385

Application
Identification of phosphoramidon as a metallo-endopeptidase inhibitor was used to characterize endothelin converting enzyme as a metallo-endopeptidase.1 Phosphoramidon increases the production of β-amyloid protein, but not amyloid precursor protein, indicating that abnormal amyloid processing in Alzheimer′s disease may be carried out by a metallo-endopeptidase.2
Biochem/physiol Actions
Potent inhibitor of thermolysin and other metallo-endopeptidases. Strongly inhibits mammalian enkephalinase. Does not inhibit trypsin, papain, chymotrypsin or pepsin. Weakly inhibits collagenase. Effective concentration 1-10 μM.
Substrates
Solubility testing at 10 mg/ml in water yields a clear, colorless to light yellow-green solution. The product is also soluble in methanol and DMSO; less soluble in ethanol and ethyl acetate; insoluble in benzene, hexane, and chloroform.Solutions can be stored in aliquots at -20 °C with an expected shelf life of at least one month.

Sigma Aldrich - 83645

Application
Identification of phosphoramidon as a metallo-endopeptidase inhibitor was used to characterize endothelin converting enzyme as a metallo-endopeptidase.1 Phosphoramidon increases the production of β-amyloid protein, but not amyloid precursor protein, indicating that abnormal amyloid processing in Alzheimer′s disease may be carried out by a metallo-endopeptidase.2
Other Notes
Naturally occurring thermolysin inhibitor3; Mode of binding4